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Regioselective addition of Grignard reagents to N-acylpyrazinium salts: synthesis of substituted 1,2-dihydropyrazines and ?5-2-oxopiperazines.

ABSTRACT: The regioselective addition of Grignard reagents to mono- and disubstituted N-acylpyrazinium salts affording substituted 1,2-dihydropyrazines in modest to excellent yields (45-100%) is described. Under acidic conditions, these 1,2-dihydropyrazines can be converted to substituted ?5-2-oxopiperazines providing a simple and efficient approach towards their preparation.

SUBMITTER: St Hilaire VR 

PROVIDER: S-EPMC6334805 | biostudies-other | 2019

REPOSITORIES: biostudies-other

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Regioselective addition of Grignard reagents to <i>N</i>-acylpyrazinium salts: synthesis of substituted 1,2-dihydropyrazines and Δ<sup>5</sup>-2-oxopiperazines.

St Hilaire Valentine R VR   Hopkins William E WE   Miller Yenteeo S YS   Dandepally Srinivasa R SR   Williams Alfred L AL  

Beilstein journal of organic chemistry 20190108

The regioselective addition of Grignard reagents to mono- and disubstituted <i>N</i>-acylpyrazinium salts affording substituted 1,2-dihydropyrazines in modest to excellent yields (45-100%) is described. Under acidic conditions, these 1,2-dihydropyrazines can be converted to substituted Δ<sup>5</sup>-2-oxopiperazines providing a simple and efficient approach towards their preparation. ...[more]